CA2475011C - Method for analysis of compounds with amino group and analytical reagent therefor - Google Patents
Method for analysis of compounds with amino group and analytical reagent therefor Download PDFInfo
- Publication number
- CA2475011C CA2475011C CA2475011A CA2475011A CA2475011C CA 2475011 C CA2475011 C CA 2475011C CA 2475011 A CA2475011 A CA 2475011A CA 2475011 A CA2475011 A CA 2475011A CA 2475011 C CA2475011 C CA 2475011C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbamate
- reagent
- amino group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
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- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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Classifications
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6806—Determination of free amino acids
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
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- Engineering & Computer Science (AREA)
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- General Physics & Mathematics (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
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| JP2002-36446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
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| CA2475011C true CA2475011C (en) | 2015-07-07 |
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| EP (3) | EP2317307B1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
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| EP2317307B1 (en) | 2002-02-14 | 2013-11-20 | Ajinomoto Co., Inc. | Method of analyzing amino- and/or imino-functional compounds, and analytical reagent |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| US7759130B2 (en) * | 2003-11-21 | 2010-07-20 | Eisai R & D Management Co., Ltd. | Mass spectrometric quantitation method for biomolecules based on metabolically labeled internal standards |
| US20070054345A1 (en) | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| JP5030586B2 (ja) * | 2004-05-26 | 2012-09-19 | 味の素株式会社 | アミノ官能性化合物の分析方法及び装置 |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| WO2006017208A1 (en) * | 2004-07-12 | 2006-02-16 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| EP1983346A4 (en) * | 2006-02-08 | 2010-03-17 | Nec Corp | METHOD FOR CLEAVING A PEPTIDE BOND AT THE C-TERMINAL END OF A PEPTIDE, AND A METHOD FOR DETERMINING THE C-TERMINAL END-ACE AMINO ACID SEQUENCE OF A PEPTIDE |
| CN101379074A (zh) * | 2006-02-08 | 2009-03-04 | 日本电气株式会社 | 修饰肽的方法和鉴定肽的方法 |
| CN104076100A (zh) * | 2007-06-29 | 2014-10-01 | 奎斯特诊断投资公司 | 用液相层析-质谱法分析体液内的氨基酸 |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| WO2009054350A1 (ja) | 2007-10-25 | 2009-04-30 | Ajinomoto Co., Inc. | 耐糖能異常の評価方法 |
| JP2011504596A (ja) * | 2007-11-26 | 2011-02-10 | ウオーターズ・テクノロジーズ・コーポレイシヨン | サンプル中の分析物を定量測定する際に使用するための内部標準および方法 |
| ES2608484T3 (es) * | 2008-02-04 | 2017-04-11 | Prozyme, Inc. | Compuestos y métodos para un marcaje rápido de N-glicanos |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| KR102002770B1 (ko) | 2011-07-21 | 2019-07-24 | 후지필름 와코 준야꾸 가부시키가이샤 | 혈장중 아미노산 분석용 표준액 |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| EP2761296B1 (en) | 2011-09-28 | 2017-08-30 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced ms signals |
| EP3557605B1 (en) | 2011-11-23 | 2021-07-14 | Quest Diagnostics Investments Incorporated | Kisspeptin-54 detection by tandem mass spectrometry |
| JP6269502B2 (ja) | 2012-11-27 | 2018-01-31 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび端末装置 |
| JP7055634B2 (ja) | 2014-10-30 | 2022-04-18 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 標識化グリコシルアミンの迅速調製およびそれを生成するグリコシル化生体分子の分析方法 |
| EP3218352B1 (en) | 2014-11-13 | 2020-08-05 | Waters Technologies Corporation | Method for liquid chromatography calibration for labeled n-glycans, method for preparing a dextran ladder calibrant and calibrant |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| US11002742B2 (en) | 2015-05-29 | 2021-05-11 | Agilent Technologies, Inc. | Compound for labeling amine-containing compounds, and its use |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| EP3449253B1 (en) | 2016-04-24 | 2025-05-28 | Waters Technologies Corporation | Isolation of glycans modified with amphipathic, strongly basic moieties, using charged surface reversed phase chromatopgraphic materials |
| US11061023B2 (en) | 2016-06-21 | 2021-07-13 | Waters Technologies Corporation | Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced MS signals |
| EP4234062A3 (en) | 2016-06-21 | 2023-10-25 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| PT3480599T (pt) | 2016-06-30 | 2024-10-18 | Ajinomoto Kk | Método de avaliação da cetose pós-parto |
| CN114839302A (zh) | 2016-07-01 | 2022-08-02 | 沃特世科技公司 | 使用分子量截留过滤和过滤器上去糖基化从复杂基质快速制备标记的葡基胺的方法 |
| CN110023763A (zh) | 2016-10-03 | 2019-07-16 | 沃特世科技公司 | 可用于lc-ms分析的标记的聚糖氨基酸复合物及其制备方法 |
| KR20200052329A (ko) * | 2017-09-08 | 2020-05-14 | 에프. 호프만-라 로슈 아게 | 질량 분석법용의 설폭사이드 기반 시약 |
| WO2019130920A1 (ja) | 2017-12-28 | 2019-07-04 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| WO2020067386A1 (ja) | 2018-09-26 | 2020-04-02 | 味の素株式会社 | 軽度認知障害の評価方法、算出方法、評価装置、算出装置、評価プログラム、算出プログラム、記録媒体、評価システムおよび端末装置 |
| CN113624862B (zh) * | 2021-07-13 | 2023-04-07 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流分析方法和试剂盒 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
| EP4702837A1 (en) | 2023-04-28 | 2026-03-04 | Ajinomoto Co., Inc. | Method for evaluating metabolic disease following calving |
| CN122459686A (zh) | 2023-12-28 | 2026-07-24 | 味之素株式会社 | 分娩后的炎症的评价方法 |
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| ATE253126T1 (de) * | 1998-08-25 | 2003-11-15 | Univ Washington | Schnelle quantitative analyse von proteinen oder proteinfunktionen in komplexen gemischen |
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| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
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| US7301018B2 (en) * | 2000-07-11 | 2007-11-27 | Japan Science And Technology Corporation | Probe for mass spectrometry of liquid sample |
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| JP3508710B2 (ja) | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| ATE405839T1 (de) * | 2000-10-23 | 2008-09-15 | Genetics Inst Llc | Isotop-kodierte ionisierung-förderende reagenzien zur hochdurchsatz protein identifikation und quantifikation mit massenspectrometrie |
| EP1330654B1 (en) * | 2000-10-23 | 2006-03-08 | Genetics Institute, LLC | Acid-labile isotope-coded extractant (alice) in mass spectometric analysis |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| EP2317307B1 (en) | 2002-02-14 | 2013-11-20 | Ajinomoto Co., Inc. | Method of analyzing amino- and/or imino-functional compounds, and analytical reagent |
| JP5030586B2 (ja) * | 2004-05-26 | 2012-09-19 | 味の素株式会社 | アミノ官能性化合物の分析方法及び装置 |
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| AU2003211941A1 (en) | 2003-09-04 |
| EP1475632B1 (en) | 2013-05-22 |
| EP1475632A4 (en) | 2008-06-25 |
| EP2317307B1 (en) | 2013-11-20 |
| US9658234B2 (en) | 2017-05-23 |
| JP2020073916A (ja) | 2020-05-14 |
| WO2003069328A1 (en) | 2003-08-21 |
| JP2016029068A (ja) | 2016-03-03 |
| EP2317307A3 (en) | 2012-03-14 |
| JP2018052972A (ja) | 2018-04-05 |
| EP2317307A2 (en) | 2011-05-04 |
| JPWO2003069328A1 (ja) | 2005-06-09 |
| US20060286673A1 (en) | 2006-12-21 |
| EP2336763A1 (en) | 2011-06-22 |
| US20160139134A1 (en) | 2016-05-19 |
| US20050079624A1 (en) | 2005-04-14 |
| CA2475011A1 (en) | 2003-08-21 |
| JP2010071995A (ja) | 2010-04-02 |
| EP1475632A1 (en) | 2004-11-10 |
| JP6278210B2 (ja) | 2018-02-14 |
| US7148069B2 (en) | 2006-12-12 |
| JP5842775B2 (ja) | 2016-01-13 |
| JP2013015537A (ja) | 2013-01-24 |
| JP5136542B2 (ja) | 2013-02-06 |
| JP7055267B2 (ja) | 2022-04-18 |
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| US9274123B2 (en) | 2016-03-01 |
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